Compound for organic electronic device, organic electronic device using same, and electronic apparatus thereof

ABSTRACT

Provided are an organic electric element comprising as a phosphorescent host material, a mixture of the compounds of Formula (1) and Formula (2), and an organic electronic device or apparatus thereof for achieving a high luminous efficiency, a low driving voltage, and an improved lifespan.

BACKGROUND Technical Field

The present invention relates to compound for organic electronicelement, organic electronic element using the same, and an electronicdevice thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenonthat converts electronic energy into light energy by using an organicmaterial. An organic electronic element using an organic light emittingphenomenon usually has a structure including an anode, a cathode, and anorganic material layer interposed therebetween. Here, in order toincrease the efficiency and stability of the organic electronic element,the organic material layer is often composed of a multi-layeredstructure composed of different materials, and for example, may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

In the case of a polycyclic compound containing a heteroatom, thedifference in properties according to the material structure is so largethat it is applied to various layers as a material of an organicelectronic element. In particular, it has characteristics of differentband gaps (HOMO, LUMO), electronical characteristics, chemicalproperties, and physical properties depending on the number of rings,fused positions and the type and arrangement of heteroatoms, thereforeapplication development for layers of various organic electronicelements using the same has been progressed.

As a representative example thereof, in the following Patent Documents 1to 4, the performance of the 5-membered cyclic compound in thepolycyclic compound has been reported depending on the hetero type,arrangement, substituent type, fused position, and the like.

-   [Patent Document 1]: U.S. Pat. No. 5,843,607-   [Patent Document 2]: Japanese Laid-Open Patent Publication No.    1999-162650-   [Patent Document 3]: Korean Published Patent Application No.    2008-0085000-   [Patent Document 4]: US Patent Publication No. 2010-0187977-   [Patent Document 5]: Korean Published Patent Application No.    2011-0018340-   [Patent Document 6]: Korean Published Patent Application No.    2009-0057711    Patent Documents 1 and 2 disclose an embodiment in which the    indolecarbazole core in which the hetero atom in the 5-membered    cyclic compound is composed only of nitrogen (N) is used, and an    aryl group substituted or unsubstituted in N of indolocarbazole is    used. However, in the prior invention 1, there exists only a simple    aryl group substituted or unsubstituted with an alkyl group, an    amino group, an alkoxy group, or the like as a substituent, so that    the effect of the substituents of the polycyclic compounds was very    poor to prove, and only the use as a hole transport material is    described, and the use thereof as a phosphorescent host material is    not described.

Patent Documents 3 and 4 disclose a compound in which pyridine,pyrimidine, triazine or the like containing an aryl group and N,respectively, were substituted for an indolecarbazole core having ahetero atom N in the same 5-membered cyclic compound as in the abovePatent Documents 1 and 2, however only the use examples forphosphorescent green host materials are described, and the performancefor other heterocyclic compounds substituted for indolecarbazole core isnot described.

In Patent Documents 5, Nitrogen (N), oxygen (O), sulfur (S), carbon andthe like are described as heteroatom in the 5-membered cyclic compound,however there are only examples using the same heteroatom in theperformance measurement data, the performance characteristics of a5-membered cyclic compound containing a different heteroatom could notbe confirmed.

Therefore, the patent document does not disclose solutions to low chargecarrier mobility and low oxidation stability of a 5-membered cycliccompound containing same heteroatom.

When the 5-membered cyclic compound molecules are generally laminated,as the adjacent π-electrons increase, they have a strong electronicalinteraction, and this is closely related to the charge carrier mobility,particularly, the same 5-membered cyclic compound of N—N type has anedge-to-face morphology as an order of arrangement of molecules whenmolecules are laminated, otherwise a different 5-membered cycliccompound with different heteroatoms has an antiparallel cofacialπ-stacking structure in which the packing structure of the molecules isopposite to each other, so that the arrangement order of the moleculesbecomes face-to-face morphology. It is reported that the steric effectof the substituent substituted on the asymmetrically arranged heteroatom N as the cause of this laminated structure causes relatively highcarrier mobility and high oxidation stability (Org. Lett. 2008, 10,1199).

In Patent Document 6, an example of using as a fluorescent host materialfor various polycyclic compounds having 7 or more membered cycliccompounds has been reported.

As described above, the fused positions, the number of rings, thearrangement of heteroatoms, and characteristic change by type of thepolycyclic compounds have not yet been sufficiently developed.

Particularly, in a phosphorescent organic electronic element using aphosphorescent dopant material, the LUMO and HOMO levels of the hostmaterial have a great influence on the efficiency and life span of theorganic electronic element, this is because the charge balance controlin the emitting layer, the quenching of the dopant, and the reduction inefficiency and life span due to light emission at the interface of thehole transport layer can be prevented, depending on whether electron andhole injection in the emitting layer can be efficiently controlled.

For fluorescent and phosphorescent host materials, recently we have beenstudying the increase of efficiency and life span of organic electronicelements using TADF (thermal activated delayed fluorescent), exciplex,etc., particularly, and many studies have been carried out to identifythe energy transfer method from the host material to the dopantmaterial.

Although there are various methods for identifying the energy transferin the emitting layer for TADF (thermally activated delayed fluorescent)and exciplex, it can be easily confirmed by the PL lifetime (TRTP)measurement method.

The TRTP (Time Resolved Transient PL) measurement method is a method ofobserving a decay time over time after irradiating the host thin filmwith a pulsed light source, and therefore it is possible to identify theenergy transfer method by observing the energy transfer and the lagtime. The TRTP measurement can distinguish between fluorescence andphosphorescence, an energy transfer method in a mixed host material, anexciplex energy transfer method, and a TADF energy transfer method.

There are various factors affecting the efficiency and life spandepending on the manner in which the energy is transferred from the hostmaterial to the dopant material, and the energy transfer method differsdepending on the material, so that the development of stable andefficient host material for organic electronic element has not yet beensufficiently developed. Therefore, development of new materials iscontinuously required, and especially development of a host material foran emitting layer is urgently required.

DETAILED DESCRIPTION OF THE INVENTION Summary

The present invention has been proposed in order to solve the problemsof the phosphorescent host material, and an object of the presentinvention is, by controlling the HOMO level of a host material of aphosphorescent emitting organic electronic element including aphosphorescent dopant, to provide a compound capable of controllingcharge balance and of improving efficiency and life span in an emittinglayer, and an organic electronic element using the same and anelectronic device thereof.

Technical Solution

In order to control the efficient hole injection in the emitting layerof the phosphorescence emitting organic electronic element, bycontaining a specific second host material in combination with aspecific first host material as a main component, it is possible toreduce the energy barrier of the emitting layer and the adjacent layer,the charge balance in the emitting layer is maximized, thereby providinghigh efficiency and high life of the organic electronic device.

The present invention provides an organic electronic element comprisinga first electrode, a second electrode, and an organic material layerformed between the first electrode and the second electrode, wherein theorganic material layer includes an emitting layer, wherein the emittinglayer includes a first host compound represented by the followingFormula (1) and a second host compound represented by the followingFormula (2).

The present invention also provides an organic electronic element usingthe compound represented by the above Formulas and an electronic devicethereof.

Effects of the Invention

By using the mixture according to the present invention as aphosphorescent host material, it is possible to achieve a high luminousefficiency and a low driving voltage of an organic electric element, andthe life span of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIG. 1 s an illustration of an organic electroluminescent deviceaccording to the present invention.

100: organic electric element, 110: substrate 120: the first electrode(anode), 130: the hole injection layer 140: the hole transport layer,141: a buffer layer 150: the emitting layer, 151: the emitting auxiliarylayer 160: the electron transport layer, 170: the electron injectionlayer 180: the second electrode (cathode)

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or“connected” to another component, the component may be directlyconnected or connected to the other component, but another component maybe “connected”, “coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, asused herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl substituted one or more of carbon atoms consisting of an alkylwith hetero atom.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”,“alkenyloxyl group” or “alkenyloxy group”, as used herein, means anoxygen radical attached to an alkenyl group, but is not limited thereto,and has 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has 6 to 60 carbon atoms, but is not limited thereto.Herein, the aryl group or arylene group means a monocyclic andpolycyclic aromatic group, and may also be formed in conjunction with anadjacent group. Examples of “aryl group” may include a phenyl group, abiphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl containing one or more of hetero atoms. Unless otherwise stated,the term “heteroaryl group” or “heteroarylene group”, as used herein,means a C2 to C60 aryl containing one or more of hetero atoms or arylenegroup, but is not limited thereto, and includes at least one ofmonocyclic and polycyclic rings, and may also be formed in conjunctionwith an adjacent group.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of monocyclic and polycyclic rings,and may include heteroaliphatic ring and/or heteroaromatic ring. Also,the heterocyclic group may also be formed in conjunction with anadjacent group. Unless otherwise stated, the term “heteroatom”, as usedherein, represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring containing SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes compound below.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Unless otherwise stated, the term “carbonyl”, as used herein, isrepresented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkylhaving 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, analkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether”, as used herein, isrepresented by —R—O—R′, wherein R or R′ may be independently hydrogen,an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbonatoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or thecombination of these.

Unless otherwise stated, the term “substituted or unsubstituted”, asused herein, means that substitution is substituted by at least onesubstituent selected from the group consisting of, but is not limitedthereto, deuterium, halogen, an amino group, a nitrile group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylaminegroup, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the presentinvention, as used herein, is applied in the same manner as thesubstituent definition according to the definition of the exponent ofthe following Formula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole substituent R¹ is linked to any oneof the carbon constituting the benzene ring, when a is an integer of 2or 3, they are respectively combined as follows, in which R¹ are thesame or different from each other, and when a is an integer of 4 to 6,and it is bonded to the carbon of the benzene ring in a similar manner,whereas the indication of hydrogen bonded to the carbon forming thebenzene ring is omitted.

Unless otherwise expressly stated, the terms “ortho”, “meta”, and “para”used in the present invention refer to the substitution positions of allsubstituents, and the ortho position indicates the position of thesubstituent immediately adjacent to the compound, for example, whenbenzene is used, it means 1 or 2 position, and the meta position is thenext substitution position of the neighbor substitution position, whenbenzene as an example stands for 1 or 3 position, and the para positionis the next substitution position of the meta position, which means 1and 4 position when benzene is taken as an example. A more detailedexample of the substitution position is as follows, and it can beconfirmed that the ortho-, and meta-position are substituted bynon-linear type and para-positions are substituted by linear type.

[Example of Ortho-Position]

[Example of Meta-Position]

[Example of Para-Position]

Hereinafter, a compound according to an aspect of the present inventionand an organic electric element comprising the same will be described.

The present invention provides an organic electric element comprising afirst electrode, a second electrode, and an organic material layerformed between the first electrode and the second electrode, wherein theorganic material layer comprises an emitting layer, wherein the emittinglayer comprises a first host compound represented by Formula (1) and asecond host compound represented by Formula (2).

{In Formulas (1) and (2),

1) Ar¹, Ar², Ar³ and Ar⁴ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one hetero atom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group;

2) c and e are each independently integers of 0 to 10, and d is aninteger of 0 to 2, and R³, R⁴ and R⁵ are the same or different from eachother, and are each independently selected from the group consisting ofdeuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and—U—N(R_(a))(R_(b)); (wherein, L′ is selected from the group consistingof a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and aC₂-C₆₀ heterocyclic; and R_(a) and R_(b) are independently selected fromthe group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and aC₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N,S, Si, or P), or in case c and e are 2 or more, and R³, R⁴ and R⁵ areeach in plural being the same or different, and a plurality of R³ or aplurality of R⁵ combine to each other to form a ring;

3) L¹, L², L³ and L⁴ are each independently selected from the groupconsisting of a single bond; a C₆-C₆₀ arylene group; and a fluorenylenegroup; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; and a C₂-C₆₀ heterocyclic group;

4) A and B are each independently a C₆-C₂₀ aryl group or a C₂-C₂₀heterocyclic group,

5) i and j are each independently 0 or 1,

with the proviso that i+j is 1 or more, and when i or j is 0, it means adirect bond,

6) X¹ and X² are each independently NR′, O, S, or CR′R″;

wherein R′ and R″ are each independently hydrogen; a C₆-C₆₀ aryl group;a fluorenyl group; a C₃-C₆₀ heterocyclic group; or a C₁-C₅₀ alkyl group;

-   -   wherein R′ and R″ may combine to each other to form a spiro,        (wherein, the aryl group, fluorenyl group, arylene group,        heterocyclic group, fused ring group, alkyl group, alkenyl        group, alkoxy group and aryloxy group may be substituted with        one or more substituents selected from the group consisting of        deuterium; halogen; a silane group substituted or unsubstituted        with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxane group;        boron group; germanium group; cyano group; nitro group;        -L′-N(R_(a))(R_(b)); a C₁-C₂₀ alkylthio group; alkoxyl group;        C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group;        C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium;        a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl        group; C₇-C₂₀ arylalkyl group; and C₈-C₂₀ arylalkenyl group;        wherein the substituents may combine each other and form a        saturated or unsaturated ring, wherein the term ‘ring’ means        C₃-C₆₀ aliphatic ring or C₆-C₆₀ aromatic ring or a C₂-C₆₀        heterocyclic ring or a fused ring formed by the combination of        thereof.)}

In addition, the present invention provides the compounds represented byFormulas (1) and (2).

The first host compound represented by Formula (1) is represented by anyone of the following Formulas (3) to (5).

{In Formulas (3) to (5),

1) L¹, L³, L⁴, Ar₂ and Ar³ are the same as defined above,

2) X³ is O or S,

3) a is an integer of 0 to 4, and b is an integer of 0 to 3, and R¹ andR² are the same or different from each other, and are each independentlyselected from the group consisting of deuterium; halogen; a C₆-C₆₀ arylgroup; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at leastone heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; aC₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or in case a and b are 2or more, R¹ and R² are each in plural being the same or different, and aplurality of R¹ or a plurality of R² combine to each other to form aring.}

The first host compound represented by Formula (1) is represented by anyone of the following Formulas (6) to (14).

{In Formulas (6) to (14),

L¹, L³, L⁴, Ar², Ar³, R¹, R², a and b are the same as defined above.}

The first host compound represented by Formula (1) is represented by anyone of the following Formulas (15) to (23).

{In Formulas (15) to (23),

L¹, L³, L⁴, Ar², Ar³, X³, R¹, R², a and b are the same as definedabove.}

The compound represented by Formula (1) is represented by any one of thefollowing Formulas (24) to (26).

{In Formulas (24) to (26),

1) L¹, L³, L⁴, Ar² and Ar³ are the same as defined above,

2) Ar⁵ and Ar⁶ are each independently selected from the group consistingof a C₆-C₆₀ aryl group; a C₂-C₆₀ heterocyclic group including at leastone heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; aC₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b))}

In Formula (1) of the present invention, L¹, L³ and L⁴ are selected fromthe group consisting of the following Formulas (A-1) to (A-12).

{In Formulas (A-1) to (A-12),

1) a′, c′, d′ and e′ are each independently integers of 0 to 4, and b′is an integer of 0 to 6, and f and g′ are each independently integers of0 to 3, and h′ is an integer of 0 to 1,

2) R⁶, R⁷ and R⁸ are the same or different from each other, and are eachindependently selected from the group consisting of deuterium; halogen;a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or incase f ‘and g’ are 2 or more, R⁶, R⁷ and R⁸ are each in plural being thesame as or different from each other, and a plurality of R⁶ or aplurality of R⁷ or adjacent R⁶ and R⁷ may combine to each other to forman aromatic or a heteroaromatic ring,

3) Y is NR′, O, S or CR′R″, and R′ and R″ are the same as defined above,

4) Z¹, Z² and Z³ are each independently CR′ or N, and at least one isN.}

In one embodiment of the present invention, the present inventionprovides an organic electric element comprising a compound wherein atleast one of L¹, L³, and L⁴ in Formula (1) is a phenyl group and issubstituted with an m (meta)-position.

The present invention provides an organic electric element wherein thesecond host compound represented by Formula (2) comprises a compoundrepresented by the following Formula (27) or (28).

{In Formulas (27) and (28),

R³, R⁴, R⁵, Ar⁴, L², c, d, e, A, B, X¹ and X² are the same as defined inFormula (2).}

The present invention also provides an organic electric elementcomprising a compound wherein A and B in Formula (2) are selected fromthe group consisting of the following Formulas (B-1) to (B-7).

{In Formulas (B-1) to (B-7),

1) Z⁴ to Z⁵⁰ are each independently CR′ or N,

2) R′ is the same as defined above,

3) * indicates the position to be condensed.}

As another example, the present invention provides a compound whereinthe second host compound represented by Formula (2) includes a compoundrepresented by any of the following Formulas (29) to (48).

{In Formulas (29) to (48),

Ar⁴, L², X¹, X², R³, R⁴, R⁵, c, d and e are the same as defined above.}

In the present invention, the second host compound represented byFormula (2) comprises any of compounds represented by the followingFormulas (49) to (56).

{In Formulas (49) to (56),

R³, R⁴, R⁵, L², Ar⁴, c, d, e, A, B, R′ and R″ are the same as definedabove.}

As a specific example of the present invention, the first host compoundrepresented by Formula (1) comprises the following Compounds 1-1′ to1-82′.

In the present invention, the second host compound represented byFormula (2) includes the following compounds 3-1 to 3-100.

Referring to the FIGURE, the organic electric element (100) according tothe present invention includes a first electrode (120) formed on asubstrate (110), a second electrode (180), and an organic material layerincluding the compound represented by Formula (1) between the firstelectrode (120) and the second electrode (180). Here, the firstelectrode (120) may be an anode (positive electrode), and the secondelectrode (180) may be a cathode (negative electrode). In the case of aninverted organic electric element, the first electrode may be a cathode,and the second electrode may be an anode.

The organic material layer may include a hole injection layer (130), ahole transport layer (140), an emitting layer (150), an electrontransport layer (160), and an electron injection layer (170) formed insequence on the first electrode (120). Here, the remaining layers exceptthe emitting layer (150) may not be formed. The organic material layermay further include a hole blocking layer, an electron blocking layer,an emitting-auxiliary layer (151), an electron transport auxiliarylayer, a buffer layer (141), etc., and the electron transport layer(160) and the like may serve as a hole blocking layer.

Although not shown, the organic electric element according to thepresent invention may further include a protective layer formed on atleast one side of the first and second electrodes, which is a sideopposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electricalcharacteristics, the interface characteristics, and the like may varydepending on which substituent is bonded at which position, thereforethe choice of core and the combination of sub-substituents associatedtherewith is also very important, and in particular, when the optimalcombination of energy levels and T1 values and unique properties ofmaterials (mobility, interfacial characteristics, etc.) of each organicmaterial layer is achieved, a long life span and high efficiency can beachieved at the same time.

The organic electroluminescent device according to an embodiment of thepresent invention may be manufactured using a PVD (physical vapordeposition) method. For example, a metal or a metal oxide havingconductivity or an alloy thereof is deposited on a substrate to form acathode, and the organic material layer including the hole injectionlayer (130), the hole transport layer (140), the emitting layer (150),the electron transport layer (160), and the electron injection layer(170) is formed thereon, and then depositing a material usable as acathode thereon can manufacture an organic electroluminescent deviceaccording to an embodiment of the present invention.

In addition, an emission auxiliary layer (151) may be further formedbetween the hole transport layer (140) and the emitting layer (150), andan electron transport auxiliary layer may be further formed between theemitting layer (150) and the electron transport layer (160).

In addition, it is preferable that at least one hole transporting bandlayer is provided between the first electrode and the light emittinglayer, and the hole transporting band layer may include a hole transportlayer, an emitting auxiliary layer, or both, and may provide an organicelectric element in which the hole transporting band layer includes thecompound represented by the formula (1).

The present invention may further include a light efficiency enhancinglayer formed on at least one of the opposite side to the organicmaterial layer among one side of the first electrode, or one of theopposite side to the organic material layer among one side of the secondelectrode.

Also, the present invention provides the organic electric elementwherein the organic material layer is formed by one of a spin coatingprocess, a nozzle printing process, an inkjet printing process, a slotcoating process, a dip coating process or a roll-to-roll process, andsince the organic material layer according to the present invention canbe formed by various methods, the scope of the present invention is notlimited by the method of forming the organic material layer.

As another specific example, the present invention provides an organicelectric element wherein the emitting layer in the organic materiallayer is a phosphorescent light emitting layer.

The compounds represented by Formula (1) and (2) are mixed in a ratio ofany one of 1:9 to 9:1 to be included in the emitting layer of theorganic material layer.

The compound represented by Formula (1) and (2) are mixed in a ratio ofany one of 1:9 to 5:5 to be included in the emitting layer of theorganic material layer. More preferably, the mixing ratio of thecompound represented by Formula (1) and (2) is 2:8 or 3:7 to be includedin the emitting layer.

The organic electric element according to an embodiment of the presentinvention may be a front emission type, a back emission type, or aboth-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization and excellent fairness, and can be manufacturedusing conventional LCD color filter technology. Various structures for awhite organic light emitting device mainly used as a backlight devicehave been proposed and patented. Representatively, there areside-by-side arrangement of the radiation part of the R (red), G (green)and B (blue), a stacking method in which R, G, and B emitting layers arelaminated on top and bottom, electroluminescence by the blue (B) organicemitting layer and, by using the light from this, a color conversionmaterial (CCM) method using a photo-luminescence of an inorganicphosphor, etc., and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising adisplay device including the organic electric element; and a controlunit for driving the display device.

According to another aspect, the present invention provides an displaydevice wherein the organic electric element is at least one of an OLED,an organic solar cell, an organic photo conductor, an organic transistor(organic TFT) and an element for monochromic or white illumination.Here, the electronic device may be a wired/wireless communicationterminal which is currently used or will be used in the future, andcovers all kinds of electronic devices including a mobile communicationterminal such as a cellular phone, a personal digital assistant (PDA),an electronic dictionary, a point-to-multipoint (PMP), a remotecontroller, a navigation unit, a game player, various kinds of TVs, andvarious kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula(1) and (2) of the present invention and preparation examples of theorganic electric element of the present invention will be described indetail by way of example, but are not limited to the following examples.

Synthesis Example 1

The final products 1 represented by Formula (1) of the present inventioncan be synthesized by reaction between Sub 1 and Sub 2 as illustrated inthe following Reaction Scheme 1.

Examples of Sub 1

Examples of Sub 1 of reaction scheme 1 are as follows, but are notlimited thereto.

Synthesis Examples of Sub 2

Sub 2 of reaction scheme 1 can be synthesized by the reaction path ofthe following reaction scheme 2, but is not limited thereto.

Examples of Sub 2-1

In a round bottom flask, Aniline (15 g, 161.1 mmol), 1-bromonaphthalene(36.7 g, 177.2 mmol), Pd₂(dba)₃ (7.37 g, 8.05 mmol), P(t-Bu)₃ (3.26 g,16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol), toluene (1690 mL) were added,and stirred at 100° C. After the reaction was completed, the reactionmixture was extracted with CH₂Cl₂ and water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was separated bysilicagel column chromatography and recrystallized to obtain 25.4 g ofSub 2-1. (Yield: 72%)

Examples of Sub 2-26

In a round bottom flask, [1,1′-biphenyl]-4-amine (15 g, 88.6 mmol),2-(4-bromophenyl)-9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol),Pd₂(dba)₃ (4.06 g, 4.43 mmol), P(t-Bu)₃ (1.8 g, 8.86 mmol), NaOt-Bu(28.1 g, 292.5 mmol), toluene (931 mL) were tested in the same manner asSub 2-1 to obtain 34.9 g of Sub 2-26. (Yield: 70%)

Examples of Sub 2-40

In a round bottom flask, naphthalen-1-amine (15 g, 104.8 mmol),2-bromodibenzo[b,d]thiophene (30.3 g, 115.2 mmol), Pd₂(dba)₃ (4.8 g,5.24 mmol), P(t-Bu)₃ (2.12 g, 10.48 mmol), NaOt-Bu (33.22 g, 345.7mmol), toluene (1100 mL) were tested in the same manner as Sub 2-1 toobtain 24.9 g of Sub 2-40. (Yield: 73%)

Examples of Sub 2-51

In a round bottom flask, 4-(dibenzo[b,d]furan-2-yl)aniline (15 g, 57.85mmol), 2-bromodibenzo[b,d]furan (15.7 g, 63.63 mmol), Pd₂(dba)₃ (2.65 g,2.89 mmol), P(t-Bu)₃ (1.17 g, 5.78 mmol), NaOt-Bu (18.35 g, 190.9 mmol),toluene (607 mL) were tested in the same manner as Sub 2-1 to obtain17.2 g of Sub 2-51. (Yield: 70%)

The following Sub 2-1 to Sub 2-52 were synthesized in the same manner asin the synthesis method, but Sub 2 is not limited thereto.

TABLE 1 compound FD-MS Sub 2-1 m/z = 219.10 (C₁₆H₁₃N = 219.28) Sub 2-2m/z = 295.14 (C₂₂H₁₇N = 295.38) Sub 2-3 m/z = 269.12 (C₂₀H₁₅N = 269.34)Sub 2-4 m/z = 169.09 (C₁₂H₁₁N = 169.22) Sub 2-5 m/z = 245.12 (C₁₈H₁₅N =245.32) Sub 2-6 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub 2-7 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-8 m/z = 345.15 (C₂₆H₁₉N = 345.44) Sub 2-9 m/z =345.15 (C₂₆H₁₉N = 345.44) Sub 2-10 m/z = 325.18 (C₂₄H₂₃N = 325.45) Sub2-11 m/z = 397.18 (C₃₀H₂₃N = 397.51) Sub 2-12 m/z = 447.20 (C₃₄H₂₅N =447.57) Sub 2-13 m/z = 371.17 (C₂₈H₂₁N = 371.47) Sub 2-14 m/z = 421.18(C₃₂H₂₃N = 421.53) Sub 2-15 m/z = 295.14 (C₂₂H₁₇N = 295.38) Sub 2-16 m/z= 397.18 (C₃₀H₂₃N = 397.51) Sub 2-17 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub2-18 m/z = 245.12 (C₁₈H₁₅N = 245.32) Sub 2-19 m/z = 321.15 (C₂₄H₁₉N =321.41) Sub 2-20 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub 2-21 m/z = 371.17(C₂₈H₂₁N = 371.47) Sub 2-22 m/z = 421.18 (C₃₂H₂₃N = 421.53) Sub 2-23 m/z= 395.17 (C₃₀H₂₁N = 395.49) Sub 2-24 m/z = 473.21 (C₃₆H₂₇N = 473.61) Sub2-25 m/z = 369.15 (C₂₈H₁₉N = 369.46) Sub 2-26 m/z = 561.25 (C₄₃H₃₁N =561.71) Sub 2-27 m/z = 411.20 (C₃₁H₂₅N = 411.54) Sub 2-28 m/z = 459.20(C₃₅H₂₅N = 459.58) Sub 2-29 m/z = 483.20 (C₃₇H₂₅N = 483.60) Sub 2-30 m/z= 375.16 (C₂₇H₂₁NO = 375.46) Sub 2-31 m/z = 475.19 (C₃₅H₂₅NO = 475.58)Sub 2-32 m/z = 575.22 (C₄₃H₂₉NO = 575.70) Sub 2-33 m/z = 533.21 (C₄₁H₂₇N= 533.66) Sub 2-34 m/z = 485.21 (C₃₇H₂₇N = 485.62) Sub 2-35 m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 2-36 m/z = 485.21 (C₃₇H₂₇N = 485.62) Sub 2-37 m/z= 499.19 (C₃₇H₂₅NO = 499.60) Sub 2-38 m/z = 439.19 (C₃₂H₂₅NO = 439.55)Sub 2-39 m/z = 335.13 (C₂₄H₁₇NO = 335.40) Sub 2-40 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-41 m/z = 427.14 (C₃₀H₂₁NS = 427.56) Sub 2-42m/z = 461.18 (C₃₄H₂₃NO = 461.55) Sub 2-43 m/z = 349.11 (C₂₄H₁₅NO₂ =349.38) Sub 2-44 m/z = 381.06 (C₂₄H₁₅NS₂ = 381.51) Sub 2-45 m/z = 457.10(C₃₀H₁₉NS₂ = 457.61) Sub 2-46 m/z = 533.13 (C₃₆H₂₃NS₂ = 533.70) Sub 2-47m/z = 353.10 (C₂₂H₁₅N₃S = 353.44) Sub 2-48 m/z = 327.0 (C₂₀H₁₃N₃S =327.40) Sub 2-49 m/z = 375.11 (C₂₆H₁₇NS = 375.48) Sub 2-50 m/z = 411.16(C₃₀H₂₁NO = 411.49) Sub 2-51 m/z = 425.14 (C₃₀H₁₉NO₂ = 425.48) Sub 2-52m/z = 475.16 (C₃₄H₂₁NO₂ = 475.54)

Synthesis Examples of Final Product Synthesis 1-1′

In a round bottom flask, di([1,1′-biphenyl]-4-yl)amine (10 g, 31.1mmol), 4-bromo-1,1′-biphenyl (8 g, 34.2 mmol), Pd₂(dba)₃ (1.42 g, 1.56mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol),toluene (330 mL) were added, and stirred at 100° C. After the reactionwas completed, the reaction mixture was extracted with CH₂Cl₂ and water.The organic layer was dried over MgSO₄ and concentrated. The resultingcompound was separated by silicagel column chromatography andrecrystallized to obtain 11.3 g of Product 1-1′. (Yield: 77%)

Synthesis 1-4′

In a round bottom flask, bis(4-(naphthalen-1-yl)phenyl)amine (10 g, 23.7mmol), 1-(4-bromophenyl)naphthalene (7.4 g, 26.1 mmol), Pd₂(dba)₃ (1.09g, 1.19 mmol), P(t-Bu)₃ (0.5 g, 2.4 mmol), NaOt-Bu (7.52 g, 78.3 mmol),toluene (250 mL) were tested in the same manner as in the above 1-1′ toobtain 11.5 g of Product 1-4′. (Yield: 78%).

Synthesis 1-10′

In a round bottom flask,N-([1,1′-biphenyl]-4-yl)[1,1′:3′,1″-terphenyl]-5′-amine (10 g, 25.2mmol), 5′-bromo-1,1′:3′,1″-terphenyl (8.56 g, 27.7 mmol), Pd₂(dba)₃(1.15 g, 1.26 mmol), P(t-Bu)₃ (0.51 g, 2.52 mmol), NaOt-Bu (7.98 g,83.02 mmol), toluene (264 mL) were tested in the same manner as in theabove 1-1′ to obtain 11.8 g of Product 1-10′. (Yield: 75%).

Synthesis 1-19′

In a round bottom flask, N-([1,1′-biphenyl]-4-yl)naphthalen-1-amine (10g, 33.6 mmol), 2-bromodibenzo[b,d]thiophene (9.8 g, 37.2 mmol),Pd₂(dba)₃ (1.55 g, 1.7 mmol), P(t-Bu)₃ (0.68 g, 3.38 mmol), NaOt-Bu(10.76 g, 112 mmol), toluene (355 mL) were tested in the same manner asin the above 1-1′ to obtain 12.3 g of Product 1-19′. (Yield: 76%).

Synthesis 1-20′

In a round bottom flask, di([1,1′-biphenyl]-3-yl)amine (10 g, 31.1mmol), 2-bromodibenzo[b,d]thiophene (9 g, 34.2 mmol), Pd₂(dba)₃ (1.42 g,1.56 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol),toluene (327 mL) were tested in the same manner as in the above 1-1′ toobtain 12.2 g of Product 1-20′. (Yield: 78%).

Synthesis 1-23′

In a round bottom flask,N-(naphthalen-1-yl)-9,9-diphenyl-9H-fluoren-2-amine (10 g, 21.8 mmol),2-bromodibenzo[b,d]thiophene (6.3 g, 23.9 mmol), Pd₂(dba)₃ (1 g, 1.09mmol), P(t-Bu)₃ (0.44 g, 2.2 mmol), NaOt-Bu (6.9 g, 71.8 mmol), toluene(230 mL) were tested in the same manner as in the above 1-1′ to obtain10.2 g of Product 1-23′. (Yield: 73%).

Synthesis 1-24′

In a round bottom flask,N-([1,1′-biphenyl]-4-yl)-9,9′-spirobi[fluoren]-2-amine (10 g, 20.7mmol), 2-bromodibenzo[b,d]thiophene (6 g, 22.7 mmol), Pd₂(dba)₃ (0.95 g,1.03 mmol), P(t-Bu)₃ (0.42 g, 2.07 mmol), NaOt-Bu (6.55 g, 68.2 mmol),toluene (220 mL) were tested in the same manner as in the above 1-1′ toobtain 10.2 g of Product 1-24′. (Yield: 74%).

Synthesis 1-29′

In a round bottom flask, N-(naphthalen-1-yl)dibenzo[b,d]thiophen-2-amine(10 g, 30.7 mmol), 2-(4-bromophenyl)dibenzo[b,d]thiophene (11.5 g, 33.8mmol), Pd₂(dba)₃ (1.41 g, 1.54 mmol), P(t-Bu)₃ (0.62 g, 3.07 mmol),NaOt-Bu (9.75 g, 101.4 mmol), toluene (325 mL) were tested in the samemanner as in the above 1-1′ to obtain 12.9 g of Product 1-29′. (Yield:72%).

Synthesis 1-30′

In a round bottom flask,N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-3-amine (10 g, 31.1 mmol),2-(3-bromophenyl)dibenzo[b,d]thiophene (11.6 g, 34.2 mmol), Pd₂(dba)₃(1.42 g, 1.55 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103mmol), toluene (330 mL) were tested in the same manner as in the above1-1′ to obtain 12.8 g of Product 1-30′. (Yield: 71%).

Synthesis 1-36′

In a round bottom flask, bis(dibenzo[b,d]thiophen-2-yl)amine (10 g, 26.2mmol), 2-bromodibenzo[b,d]thiophene (7.59 g, 28.8 mmol), Pd₂(dba)₃ (1.2g, 1.31 mmol), P(t-Bu)₃ (0.53 g, 2.62 mmol), NaOt-Bu (8.31 g, 86.5mmol), toluene (275 mL) were tested in the same manner as in the above1-1′ to obtain 11.4 g of Product 1-36′. (Yield: 77%).

Synthesis 1-49′

In a round bottom flask, di([1,1′-biphenyl]-4-yl)amine (10 g, 31.1mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (11.1 g, 34.2 mmol), Pd₂(dba)₃(1.42 g, 1.56 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103mmol), toluene (330 mL) were tested in the same manner as in the above1-1′ to obtain 13.3 g of Product 1-49′. (Yield: 76%).

Synthesis 1-51′

In a round bottom flask, N-(4-(naphthalen-1-yl)phenyl)naphthalen-2-amine(10 g, 28.9 mmol),2-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan (14 g, 32mmol), Pd₂(dba)₃ (1.33 g, 1.45 mmol), P(t-Bu)₃ (0.59 g, 2.9 mmol),NaOt-Bu (9.2 g, 95.5 mmol), toluene (310 mL) were tested in the samemanner as in the above 1-1′ to obtain 14.5 g of Product 1-51′. (Yield:71%).

Synthesis 1-59′

In a round bottom flask,N-([1,1′-biphenyl]-4-yl)benzo[4,5]thieno[3,2-d]pyrimidin-2-amine (10 g,28.3 mmol), 4-(4-bromophenyl)dibenzo[b,d]furan (10.1 g, 31.1 mmol),Pd₂(dba)₃ (1.3 g, 1.41 mmol), P(t-Bu)₃ (0.57 g, 2.83 mmol), NaOt-Bu(8.98 g, 93.4 mmol), toluene (300 mL) were tested in the same manner asin the above 1-1′ to obtain 12.3 g of Product 1-59′. (Yield: 73%).

Synthesis 1-71′

In a round bottom flask, di([1,1′-biphenyl]-4-yl)amine (10 g, 31.1mmol), 2-(4-bromophenyl)-9,9′-spirobi[fluorene] (16.1 g, 34.2 mmol),Pd₂(dba)₃ (1.42 g, 1.56 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu(9.87 g, 102.7 mmol), toluene (330 mL) were tested in the same manner asin the above 1-1′ to obtain 15.5 g of Product 1-71′. (Yield: 70%).

Synthesis 1-75′

In a round bottom flask,N-(4-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-[1,1′-biphenyl]-4-amine (10g, 17.8 mmol), 3-bromo-9,9-diphenyl-9H-fluorene (7.78 g, 19.6 mmol),Pd₂(dba)₃ (0.82 g, 0.89 mmol), P(t-Bu)₃ (0.36 g, 1.78 mmol), NaOt-Bu(5.65 g, 58.75 mmol), toluene (190 mL) were tested in the same manner asin the above 1-1′ to obtain 11.3 g of Product 1-75′. (Yield: 72%).

TABLE 2 compound FD-MS 1-1′ m/z = 473.21 (C₃₆H₂₇N = 473.61) 1-2′ m/z =523.23 (C₄₀H₂₉N = 523.66) 1-3′ m/z = 573.25 (C₄₄H₃₁N = 573.72) 1-4′ m/z= 623.26 (C₄₈H₃₃N = 623.78) 1-5′ m/z = 447.20 (C₃₄H₂₅N = 447.57) 1-6′m/z = 371.17 (C₂₈H₂₁N = 371.47) 1-7′ m/z = 471.20 (C₃₆H₂₅N = 471.59)1-8′ m/z = 521.21 (C₄₀H₂₇N = 521.65) 1-9′ m/z = 549.25 (C₄₂H₃₁N =549.70) 1-10′ m/z = 625.28 (C₄₈H₃₅N = 625.80) 1-11′ m/z = 675.29(C₅₂H₃₇N = 675.86) 1-12′ m/z = 473.21 (C₃₆H₂₇N = 473.61) 1-13′ m/z =523.23 (C₄₀H₂₉N = 523.66) 1-14′ m/z = 623.26 (C₄₈H₃₃N = 623.78) 1-15′m/z = 549.25 (C₄₂H₃₁N = 549.70) 1-16′ m/z = 625.28 (C₄₈H₃₅N = 625.80)1-17′ m/z = 503.17 (C₃₆H₂₅NS = 503.66) 1-18′ m/z = 603.20 (C₄₄H₂₉NS =603.77) 1-19′ m/z = 477.16 (C₃₄H₂₃NS = 477.62) 1-20′ m/z = 503.17(C₃₆H₂₅NS = 503.66) 1-21′ m/z = 451.14 (C₃₂H₂₁NS = 451.58) 1-22′ m/z =593.22 (C₄₃H₃₁NS = 593.78) 1-23′ m/z = 641.22 (C₄₇H₃₁NS = 641.82) 1-24′m/z = 665.22 (C₄₉H₃₁NS = 665.84) 1-25′ m/z = 503.17 (C₃₆H₂₅NS = 503.66)1-26′ m/z = 655.23 (C₄₈H₃₃NS = 655.85) 1-27′ m/z = 695.26 (C₅₁H₃₇NS =695.91) 1-28′ m/z = 593.18 (C₄₂H₂₇NOS = 593.73) 1-29′ m/z = 583.14(C₄₀H₂₅NS₂ = 583.76) 1-30′ m/z = 579.20 (C₄₂H₂₉NS = 579.75) 1-31′ m/z =685.19 (C₄₈H₃₁NS₂ = 685.90) 1-32′ m/z = 719.23 (C₅₂H₃₃NOS = 719.89)1-33′ m/z = 629.22 (C₄₆H₃₁NS = 629.81) 1-34′ m/z = 629.22 (C₄₆H₃₁NS =629.81) 1-35′ m/z = 603.20 (C₄₄H₂₉NS = 603.77) 1-36′ m/z = 563.08(C₃₆H₂₁NS₃ = 563.75) 1-37′ m/z = 639.11 (C₄₂H₂₅NS₃ = 639.85) 1-38′ m/z =715.15 (C₄₈H₂₉NS₃ = 715.95) 1-39′ m/z = 791.18 (C₅₄H₃₃NS₃ = 792.04)1-40′ m/z = 607.16 (C₄₂H₂₅NO₂S = 607.72) 1-41′ m/z = 633.21 (C₄₅H₃₁NOS =633.80) 1-42′ m/z = 733.24 (C₅₃H₃₅NOS = 733.92) 1-43′ m/z = 883.29(C₆₅H₄₁NOS = 884.09) 1-44′ m/z = 585.13 (C₃₈H₂₃N₃S₂ = 585.74) 1-45′ m/z= 553.19 (C₄₀H₂₇NS = 553.71) 1-46′ m/z = 603.20 (C₄₄H₂₉NS = 603.77)1-47′ m/z = 841.28 (C₆₃H₃₉NS = 842.06) 1-48′ m/z = 563.22 (C₄₂H₂₉NO =563.69) 1-49′ m/z = 563.22 (C₄₂H₂₉NO = 563.69) 1-50′ m/z = 613.24(C₄₆H₃₁NO = 613.76) 1-51′ m/z = 703.29 (C₅₃H₃₇NO = 703.87) 1-52′ m/z =587.22 (C₄₄H₂₉NO = 587.71) 1-53′ m/z = 639.26 (C₄₈H₃₃NO = 639.78) 1-54′m/z = 639.26 (C₄₈H₃₃NO = 639.78) 1-55′ m/z = 653.24 (C₄₈H₃₁NO₂ = 653.77)1-56′ m/z = 603.26 (C₄₅H₃₃NO = 603.75) 1-57′ m/z = 727.29 (C₅₅H₃₇NO =727.89) 1-58′ m/z = 725.27 (C₅₅H₃₅NO = 725.87) 1-59′ m/z = 595.17(C₄₀H₂₅N₃OS = 595.71) 1-60′ m/z = 567.26 (C₄₂H₃₃NO = 567.72) 1-61′ m/z =611.22 (C₄₆H₂₉NO = 611.73) 1-62′ m/z = 617.18 (C₄₄H₂₇NOS = 617.76) 1-63′m/z = 637.24 (C₄₈H₃₁NO = 637.77) 1-64′ m/z = 667.21 (C₄₈H₂₉NO₃ = 667.75)1-65′ m/z = 767.25 (C₅₆H₃₃NO₃ = 767.87) 1-66′ m/z = 681.27 (C₅₀H₃₅NO₂ =681.82) 1-67′ m/z = 658.22 (C₄₅H₃₀N₄S = 658.82) 1-68′ m/z = 655.23(C₄₈H₃₃NS = 655.86) 1-69′ m/z = 744.26 (C₅₄H₃₆N₂S = 744.96) 1-70′ m/z =784.27 (C₅₅H₃₆N₄S = 784.98) 1-71′ m/z = 553.19 (C₄₀H₂₇NS = 553.72) 1-72′m/z = 553.19 (C₄₀H₂₇NS = 553.72) 1-73′ m/z = 543.20 (C₃₉H₂₉NS = 543.73)1-74′ m/z = 671.21 (C₄₈H₃₀FNS = 671.83) 1-75′ m/z = 641.25 (C₄₆H₃₁N₃O =641.77) 1-76′ m/z = 639.26 (C₄₈H₃₃NO = 639.80) 1-77′ m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 1-78′ m/z = 614.24 (C₄₅H₃₀N₂O = 614.75) 1-79′ m/z =587.22 (C₄₄H₂₉NO = 587.72) 1-80′ m/z = 613.24 (C₄₆H₃₁NO = 613.76) 1-81′m/z = 543.26 (C₄₀H₃₃NO = 543.71) 1-82′ m/z = 667.25 (C₄₉H₃₃NO₂ = 667.81)

Synthesis Examples 2

The final product 2 represented by Formula (2) of the present inventionis prepared by reacting Sub 3 and Sub 4 as shown in the followingReaction Scheme 3.

Synthesis Example of Sub 3

Sub 3 of Reaction Scheme 3 can be synthesized by the reaction path ofthe following Reaction Scheme 4, but is not limited thereto.

Synthesis Examples of Sub 3(1)

Synthesis Method of Sub 3-2-1

After Sub 3-1-1 (40.8 g, 155 mmol), bis(pinacolato)diboron (43.4 g, 171mmol), KOAc (46 g, 466 mmol), PdCl₂(dppf) (3.8 g, 4.7 mmol) weredissolved in DMF (980 mL), and refluxed at 120° C. for 12 hours. Whenthe reaction was completed, the temperature of the reaction was cooledto room temperature, extracted with CH₂Cl₂ and wiped with water. Theorganic layer was dried over MgSO₄ and concentrated. The resultingcompound was recrystallized by CH₂Cl₂ and methanol solvent to obtain Sub3-2-1. (38.5 g, 80%)

Synthesis Method of Sub 3-4-1

Sub 3-2-1 (34.4 g, 111 mmol), Sub 3-3-1 (33.5 g, 133 mmol), K₂CO₃ (46.03g, 333 mmol), Pd(PPh₃)₄ (7.7 g, 6.66 mmol) were added in a round bottomflask and THF (490 mL) and water (245 mL) were added to dissolve andrefluxed at 80° C. for 12 hours. When the reaction was completed, thetemperature of the reaction was cooled to room temperature, extractedwith CH₂Cl₂ and wiped with water. The organic layer was dried over MgSO₄and concentrated. The resulting compound was separated by silicagelcolumn chromatography to obtain Sub 3-4-1. (31.2 g, 79%)

Synthesis Method of Sub 3(1)

Sub 3-4-1 (20 g, 56.3 mmol) and triphenylphosphine (37 g, 141 mmol) weredissolved in o-dichlorobenzene (235 mL) and refluxed for 24 hours. Whenthe reaction was completed, the solvent was removed using reducedpressure distillation. The resulting compound was separated by silicagelcolumn chromatography and recrystallized to obtain Sub 3(1) (14.7 g,81%).

Synthesis Example of Sub 3(2)

Synthesis Method of Sub 3-2-2

Sub 3-1-2 (40.8 g, 155 mmol) was carried out in the same manner as inSub 3-2-1 to give the product Sub 3-2-2 (37.5 g, 78%).

Synthesis Method of Sub 3-4-2

Sub 3-2-2 (34.4 g, 111 mmol) and Sub 3-3-1 (33.5 g, 133 mmol) werecarried out in the same manner as in Sub 3-4-1 to give the product Sub3-4-2 (30.4 g, 77%).

Synthesis Method of Sub 3(2)

Sub 3-4-2 (20 g, 56.3 mmol) was carried out in the same manner as in Sub3(1) to give the product Sub 3(2) (14.4 g, 79%).

Synthesis Example of Sub 3(7)

Synthesis Method of Sub 3-2-3

Sub 3-1-3 (57.7 g, 155 mmol) was carried out in the same manner as inSub 3-2-1 to give the product Sub 3-2-3 (57.7 g, 78%).

Synthesis Method of Sub 3-4-3

Sub 3-2-3 (46.5 g, 111 mmol) and Sub 3-3-2 (26.9 g, 133 mmol) werecarried out in the same manner as in Sub 3-4-1 to give the product Sub3-4-3 (37.3 g, 81%).

Synthesis Method of Sub 3(7)

Sub 3-4-3 (23.3 g, 56.3 mmol) was carried out in the same manner as inSub 3(1) to give the product Sub 3(7) (17.9 g, 83%).

Synthesis Example of Sub 3(13)

Synthesis Method of Sub 3-2-4

Sub 3-1-4 (53.8 g, 155 mmol) was carried out in the same manner as inSub 3-2-1 to give the product Sub 3-2-4 (46.4 g, 76%).

Synthesis Method of Sub 3-4-4

Sub 3-2-4 (43.8 g, 111 mmol) and Sub 3-3-2 (26.9 g, 133 mmol) werecarried out in the same manner as in Sub 3-4-1 to give the product Sub3-4-4 (34.6 g, 80%).

Synthesis Method of Sub 3(13)

Sub 3-4-4 (21.9 g, 56.3 mmol) was carried out in the same manner as inSub 3(1) to give the product Sub 3(13) (16.3 g, 81%).

Synthesis Example of Sub 3(26)

Synthesis Method of Sub 3-2-5

Sub 3-1-5 (50.1 g, 155 mmol) was carried out in the same manner as inSub 3-2-1 to give the product Sub 3-2-5 (44.2 g, 76%).

Synthesis Method of Sub 3-4-5

Sub 3-2-5 (41.1 g, 111 mmol) and Sub 3-3-3 (33.5 g, 133 mmol) werecarried out in the same manner as in Sub 3-4-1 to give the product Sub3-4-5 (37.4 g, 81%).

Synthesis Method of Sub 3(26)

Sub 3-4-5 (23.4 g, 56.3 mmol) was carried out in the same manner as inSub 3(1) to give the product Sub 3(26) (17.9 g, 83%).

Synthesis Example of Sub 3(39)

Synthesis Method of Sub 3-2-6

Sub 3-1-6 (57.7 g, 155 mmol) was carried out in the same manner as inSub 3-2-1 to give the product Sub 3-2-6 (51.3 g, 79%).

Synthesis Method of Sub 3-4-6

Sub 3-2-6 (46.5 g, 111 mmol) and Sub 3-3-4 (33.5 g, 133 mmol) werecarried out in the same manner as in Sub 3-4-1 to give the product Sub3-4-6 (41.2 g, 80%).

Synthesis Method of Sub 3(39)

Sub 3-4-6 (26.2 g, 56.3 mmol) was carried out in the same manner as inSub 3(1) to give the product Sub 3(39) (19.7 g, 81%).

Synthesis Example of Sub 3(45)

Synthesis Method of Sub 3-2-7

Sub 3-1-7 (46.1 g, 155 mmol) was carried out in the same manner as inSub 3-2-1 to give the product Sub 3-2-7 (43.2 g, 81%).

Synthesis Method of Sub 3-4-7

Sub 3-2-7 (38.2 g, 111 mmol) and Sub 3-3-3 (33.5 g, 133 mmol) werecarried out in the same manner as in Sub 3-4-1 to give the product Sub3-4-7 (36.7 g, 85%).

Synthesis Method of Sub 3(45)

Sub 3-4-7 (21.9 g, 56.3 mmol) was carried out in the same manner as inSub 3(1) to give the product Sub 3(45) (16.3 g, 81%).

Examples of Sub 3 include, but are not limited to, the followings.

TABLE 3 compound FD-MS Sub 3(1) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub3(2) m/z = 323.08 (C₂₂H1₃NS = 323.41) Sub 3(3) m/z = 307.10 (C₂₂H₁₃NO =307.34) Sub 3(4) m/z = 307.10 (C₂₂H₁₃NO = 307.34) Sub 3(5) m/z = 333.15(C₂₅H₁₉N = 333.43) Sub 3(6) m/z = 382.15 (C₂₈H₁₈N₂ = 382.46) Sub 3(7)m/z = 382.15 (C₂₈H₁₈N₂ = 382.47) Sub 3(8) m/z = 323.08 (C₂₂H₁₃NS =323.41) Sub 3(9) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3(10) m/z = 383.17(C₂₉H₂₁N = 383.49) Sub 3(11) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3(12)m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3(13) m/z = 357.12 (C₂₆H₁₅NO =357.41) Sub 3(14) m/z = 333.15 (C₂₅H₁₉N = 333.43) Sub 3(15) m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3(16) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3(17)m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3(18) m/z = 373.09 (C₂₆H₁₅NS =373.47) Sub 3(19) m/z = 407.13 (C₃₀H₁₇NO = 407.47) Sub 3(20) m/z =433.18 (C₃₃H₂₃N = 433.55) Sub 3(21) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub3(22) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3(23) m/z = 662.25 (C₄₈H₃₀N₄= 662.80) Sub 3(24) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3(25) m/z =357.12 (C₂₆H₁₅NO = 357.41) Sub 3(26) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub3(27) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3(28) m/z = 323.08 (C₂₂H₁₃NS= 323.41) Sub 3(29) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3(30) m/z =455.17 (C₃₅H₂₁N = 455.56) Sub 3(31) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub3(32) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3(33) m/z = 307.10 (C₂₂H₁₃NO= 307.35) Sub 3(34) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3(35) m/z =432.16 (C₃₂H₂₀N₂ = 439.53) Sub 3(36) m/z = 373.09 (C₂₆H₁₅NS = 373.47)Sub 3(37) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3(38) m/z = 383.17(C₂₉H₂₁N = 383.49) Sub 3(39) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3(40)m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3(41) m/z = 357.12 (C₂₆H₁₅NO =357.41) Sub 3(42) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3(43) m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub 3(44) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3(45)m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3(46) m/z = 505.18 (C₃₉H₂₃N =505.62) Sub 3(47) m/z = 382.15 (C₂₈H₁₈N₂ = 382.47) Sub 3(48) m/z =323.08 (C₂₂H₁₃NS = 323.41) Sub 3(49) m/z = 307.10 (C₂₂H₁₃NO = 307.35)Sub 3(50) m/z = 333.15 (C₂₅H₁₉N = 333.43) Sub 3(51) m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub 3(52) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3(53)m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3(54) m/z = 457.18 (C₃₅H₂₃N =457.58) Sub 3(55) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3(56) m/z =373.09 (C₂₆H₁₅NS = 373.47) Sub 3(57) m/z = 357.12 (C₂₆H₁₅NO = 357.41)Sub 3(58) m/z = 383.17 (C₂₉H₂₁N = 383.49)

Examples of Sub 4

Examples of Sub 4 include, but are not limited to, the followings.

TABLE 4 compound FD-MS Sub 4-1 m/z = 155.96 (C₆H₅Br = 157.01) Sub 4-2m/z = 205.97 (C₁₀H₇Br = 207.07) Sub 4-3 m/z = 205.97 (C₁₀H₇Br = 207.07)Sub 4-4 m/z = 231.99 (C₁₂H₉Br = 233.10) Sub 4-5 m/z = 309.02 (C₁₇H₁₂BrN= 310.19) Sub 4-6 m/z = 311.01 (C₁₅H₁₀BrN₃ = 312.16) Sub 4-7 m/z =310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 4-8 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18)Sub 4-9 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 4-10 m/z = 387.04(C₂₁H₁₄BrN₃ = 388.26) Sub 4-11 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub4-12 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 4-13 m/z = 348.03(C₁₉H₁₃BrN₂ = 349.22) Sub 4-14 m/z = 271.99 (C₁₃H₉BrN₂ = 273.13) Sub4-15 m/z = 283.99 (C₁₄H₉BrN₂ = 285.14) Sub 4-16 m/z = 374.01(C₂₀H₁₁BrN₂O = 375.22) Sub 4-17 m/z = 400.06 (C₂₃H₁₇BrN₂ = 401.30) Sub4-18 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub 4-19 m/z = 476.09(C₂₉H₂₁BrN₂ = 477.39) Sub 4-20 m/z = 284.99 (C₁₃H₈BrN₃ = 286.13) Sub4-21 m/z = 289.03 (C₁₄H₄D₅BrN₂ = 290.2) Sub 4-22 m/z = 284.99 (C₁₃H₈BrN₃= 286.13) Sub 4-23 m/z = 375.00 (C₁₉H₁₀BrN₃O = 376.2) Sub 4-24 m/z =401.05 (C₂₂H₁₆BrN₃ = 402.29) Sub 4-25 m/z = 296.02 (C₁₆H₉ClN₂S = 296.77)Sub 4-26 m/z = 322.03 (C₁₈H₁₁ClN₂S = 322.81) Sub 4-27 m/z = 322.03(C₁₈H₁₁ClN₂S = 322.81) Sub 4-28 m/z = 168.98 (C₇H₄ClNS = 169.63) Sub4-29 m/z = 168.98 (C₇H₄ClNS = 169.63)) Sub 4-30 m/z = 169.97 (C₆H₃ClN₂S= 170.62) Sub 4-31 m/z = 246.00 (C₁₂H₇ClN₂S = 246.72) Sub 4-32 m/z =322.03 (C₁₈H₁₁ClN₂S = 322.81) Sub 4-33 m/z = 322.03 (C₁₈H₁₁ClN₂S =322.81) Sub 4-34 m/z = 168.98 (C₇H₄ClNS = 169.63) Sub 4-35 m/z = 168.98(C₇H₄ClNS = 169.63)) Sub 4-36 m/z = 169.97 (C₆H₃ClN₂S = 170.62) Sub 4-37m/z = 229.04 (C₁₂H₈ClN₃ = 229.67) Sub 4-38 m/z = 279.06 (C₁₆H₁₀ClN₃ =279.72) Sub 4-39 m/z = 305.07 (C₁₈H₁₂ClN₃ = 305.76) Sub 4-40 m/z =228.05 (C₁₃H₉ClN₂ = 228.68) Sub 4-41 m/z = 228.05 (C₁₃H₉ClN₂ = 228.68)Sub 4-42 m/z = 229.04 (C₁₂H₈ClN₃ = 229.67) Sub 4-43 m/z = 229.04(C₁₂H₈ClN₃ = 229.67) Sub 4-44 m/z = 279.06 (C₁₆H₁₀ClN₃ = 279.72) Sub4-45 m/z = 305.07 (C₁₈H₁₂ClN₃ = 305.76) Sub 4-46 m/z = 228.05 (C₁₃H₉ClN₂= 228.68) Sub 4-47 m/z = 228.05 (C₁₃H₉ClN₂ = 228.68) Sub 4-48 m/z =229.04 (C₁₂H₈ClN₃ = 229.67) Sub 4-49 m/z = 330.1 (C₂₀H₁₁ClN₂O = 330.77)Sub 4-50 m/z = 372.05 (C₂₂H₁₃ClN₂S = 372.87) Sub 4-51 m/z = 366.09(C₂₄H₁₅ClN₂ = 366.85) Sub 4-52 m/z = 340.08 (C₂₂H₁₃ClN₂ = 340.81) Sub4-53 m/z = 290.06 (C₁₈H₁₁ClN₂ = 290.75) Sub 4-54 m/z = 340.08(C₂₂H₁₃ClN₂ = 340.81)

Synthesis of Final Product 2 Synthesis Example of 3-6

After Sub 3(1) (15.3 g, 47.3 mmol) was placed in a round bottom flaskand dissolved in toluene (500 mL), and Sub 4-15 (14.8 g, 52.0 mmol),Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.1 g, 5.2 mmol), NaOt-Bu (15 g,156.1 mmol) were added and refluxed at 100° C. After the reaction wascompleted, the reaction mixture was extracted with CH₂Cl₂ and water. Theorganic layer was dried over MgSO₄ and concentrated. The resultingcompound was separated by silicagel column chromatography andrecrystallized to obtain 19 g of Product. (Yield: 76%)

Synthesis Example of 3-1

Sub 3(7) (18.1 g, 47.3 mmol), toluene (500 mL), Sub 4-1 (8.2 g, 52.0mmol), Pd₂(dba)₃ (2.0 g, 2.2 mmol), P(t-Bu)₃ (0.9 g, 4.4 mmol), NaOt-Bu(12.7 g, 132 mmol) were added, the same procedure as described in thesynthesis method of 3-6 was carried out to obtain 16.7 g of the finalproduct. (Yield: 77%).

Synthesis Example of 3-7

Sub 3(1) (15.3 g, 47.3 mmol), Sub 4-25 (15.4 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 19.6 g of the final product. (Yield: 71%).

Synthesis Example of 3-8

Sub 3(1) (15.3 g, 47.3 mmol), Sub 4-53 (15.1 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 19.9 g of the final product. (Yield: 73%).

Synthesis Example of 3-11

Sub 3(13) (16.9 g, 47.3 mmol), Sub 4-55 (16.1 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 19.4 g of the final product. (Yield: 70%).

Synthesis Example of 3-16

Sub 3(17) (18.1 g, 47.2 mmol), Sub 4-56 (16.7 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 21 g of the final product. (Yield: 71%).

Synthesis Example of 3-17

Sub 3(59) (20.5 g, 47.4 mmol), Sub 4-57 (13.7 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 20.1 g of the final product. (Yield: 69%).

Synthesis Example of 3-47

Sub 3(45) (16.9 g, 47.3 mmol), Sub 4-58 (14.6 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 10.6 g of the final product. (Yield: 74%).

Synthesis Example of 3-52

Sub 3(50) (15.8 g, 47.4 mmol), Sub 4-12 (20.2 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 20.6 g of the final product. (Yield: 70%).

Synthesis Example of 3-70

Sub 3(60) (17.7 g, 47.4 mmol), Sub 4-59 (17.8 g, 52.0 mmol) were added,the same procedure as described in the synthesis method of 3-6 wascarried out to obtain 22.8 g of the final product. (Yield: 73%).

TABLE 5 compound FD-MS 3-1 m/z = 458.18 (C₃₄H₂₂N₂ = 458.56) 3-2 m/z =449.12 (C₃₂H₁₉NS = 449.57) 3-3 m/z = 433.15 (C₃₂H₁₉NO = 433.51) 3-4 m/z= 535.23 (C₄₁H₂₉N = 535.69) 3-5 m/z = 399.11 (C₂₈H₁₇NS = 399.51) 3-6 m/z= 527.15 (C₃₆H₂₁N₃S = 527.65) 3-7 m/z = 583.12 (C₃₈H₂₁N₃S₂ = 583.73) 3-8m/z = 577.16 (C₄₀H₂₃N₃S = 577.71) 3-9 m/z = 627.18 (C₄₄H₂₅N₃S = 627.77)3-10 m/z = 475.14 (C₃₄H₂₁NS = 475.61) 3-11 m/z = 585.21 (C₄₄H₂₇NO =585.71) 3-12 m/z = 509.21 (C₃₉H₂₇N = 509.65) 3-13 m/z = 509.19 (C₃₇H₂₃N₃= 509.61) 3-14 m/z = 451..11 (C₃₀H₁₇N₃S = 451.55) 3-15 m/z = 588.20(C₄₁H₂₄N₄O = 588.67) 3-16 m/z = 624.26 (C₄₇H₃₂N₂ = 624.79) 3-17 m/z =614.18 (C₄₄H₂₆N₂S = 614.77) 3-18 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-19m/z = 573.17 (C₄₂H₂₃NO₂ = 573.65) 3-20 m/z = 664.26 (C₄₈H₃₂N₄ = 664.81)3-21 m/z = 624.26 (C₄₇H₃₂N₂ = 624.79) 3-22 m/z = 603.18 (C₄₂H₂₅N₃S =603.74) 3-23 m/z = 664.23 (C₄₇H₂₈N₄O = 664.77) 3-24 m/z = 737.28(C₅₅H₃₅N₃ = 737.91) 3-25 m/z = 738.28 (C₅₄H₃₄N₄ = 738.89) 3-26 m/z =679.21 (C₄₈H₂₉N₃S = 679.84) 3-27 m/z = 625.22 (C₄₅H₂₇N₃O = 625.73) 3-28m/z = 575.24 (C₄₂H₂₉N₃ = 575.72) 3-29 m/z = 508.19 (C₃₈H₂₄N₂ = 508.62)3-30 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-31 m/z = 433.15 (C₃₂H₁₉NO =433.51) 3-32 m/z = 531.20 (C₄₁H₂₅N = 531.66) 3-33 m/z = 608.23 (C₄₆H₂₈N₂= 608.74) 3-34 m/z = 475.14 (C₃₄H₂₁NS = 475.61) 3-35 m/z = 384.13(C₂₇H₁₆N₂O = 384.44) 3-36 m/z = 614.25 (C₄₄H₃₀N₄ = 614.75) 3-37 m/z =508.19 (C₃₈H₂₄N₂ = 508.62) 3-38 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-39m/z = 433.15 (C₃₂H₁₉NO = 433.51) 3-40 m/z = 459.20 (C₃₅H₂₅N = 459.59)3-41 m/z = 663.24 (C₄₇H₂₉N₅ = 663.78) 3-42 m/z = 603.18 (C₄₂H₂₅N₃S =603.74) 3-43 m/z = 587.20 (C₄₂H₂₅N₃O = 587.68) 3-44 m/z = 613.25(C₄₅H₃₁N₃ = 613.76) 3-45 m/z = 662.25 (C₄₈H₃₀N₄ = 662.80) 3-46 m/z =577.16 (C₄₀H₂₃N₃S = 577.71) 3-47 m/z = 601.18 (C₄₂H₂₃N₃O₂ = 601.67) 3-48m/z = 759.27 (C₅₇H₃₃N₃ = 759.91) 3-49 m/z = 589.22 (C₄₂H₂₆N₄ = 586.70)3-50 m/z = 630.19 (C₄₃H₂₆N₄S = 630.77) 3-51 m/z = 613.22 (C₄₄H₂₇N₃O =613.72) 3-52 m/z = 639.27 (C₄₇H₃₃N₃ = 639.80) 3-53 m/z = 508.19(C₃₈H₂₄N₂ = 508.62) 3-54 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-55 m/z =433.15 (C₃₂H₁₉NO = 433.51) 3-56 m/z = 609.25 (C₄₇H₃₁N = 609.77) 3-57 m/z= 663.24 (C₄₇H₂₉N₅ = 663.78) 3-58 m/z = 604.17 (C₄₁H₂₄N₄S = 604.73) 3-59m/z = 587.20 (C₄₂H₂₅N₃O = 587.68) 3-60 m/z613.25 (C₄₅H₃₁N₃ = 613.76)3-61 m/z = 527.15 (C₃₆H₂₁N₃S = 527.65) 3-62 m/z = 603.18 (C₄₂H₂₅N₃S =603.74) 3-63 m/z = 511.17 (C₃₆H₂₁N₃O = 511.58) 3-64 m/z = 587.24(C₄₃H₂₉N₃ = 587.73) 3-65 m/z = 692.20 (C₄₈H₂₈N₄S = 692.84) 3-66 m/z =577.16 (C₄₀H₂₃N₃S = 577.71) 3-67 m/z = 561.18 (C₄₀H₂₃N₃O = 561.64) 3-68m/z = 653.19 (C₄₆H₂₇N₃S = 653.80) 3-69 m/z = 736.26 (C₅₄H₃₂N₄ = 736.88)3-70 m/z = 677.19 (C₄₈H₂₇N₃S = 677.83) 3-71 m/z = 687.23 (C₅₀H₂₉N₃O =687.80) 3-72 m/z = 743.24 (C₅₃H₃₃N₃S = 743.93) 3-73 m/z = 703.21(C₅₀H₂₉N₃S = 703.86) 3-74 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 3-75 m/z =735.18 (C₅₀H₂₉N₃S₂ = 735.92) 3-76 m/z = 759.18 (C₅₂H₂₉N₃S₂ = 759.95)3-77 m/z = 475.14 (C₃₄H₂₁NS = 475.61) 3-78 m/z = 616.20 (C₄₄H₂₈N₂S =616.78) 3-79 m/z = 710.16 (C₄₇H₂₆N₄S₂ = 710.87) 3-80 m/z = 818.25(C₅₈H₃₄N₄S = 819.00) 3-81 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 3-82 m/z =809.20 (C₅₆H₃₁N₃S₂ = 810.01) 3-83 m/z = 659.15 (C₄₄H₂₅N₃S₂ = 659.83)3-84 m/z = 583.21 (C₄₀H₂₉N₃S = 583.75) 3-85 m/z = 844.27 (C₆₀H₃₆N₄S =845.04) 3-86 m/z = 667.17 (C₄₆H₂₅N₃OS = 667.79) 3-87 m/z = 703.23(C₅₀H₂₉N₃O₂ = 703.80) 3-88 m/z = 629.21 (C₄₄H₂₇N₃O₂ = 629.72) 3-89 m/z =473.18 (C₃₅H₂₃NO = 473.58) 3-90 m/z = 600.22 (C₄₄H₂₈N₂O = 600.72) 3-91m/z = 858.25 (C₆₀H₃₄N₄OS = 859.02) 3-92 m/z = 792.26 (C₅₅H₃₂N₆O =792.90) 3-93 m/z = 514.24 (C₃₈H₃₀N₂ = 514.67) 3-94 m/z = 701.28(C₅₂H₃₅N₃ = 701.87) 3-95 m/z = 700.26 (C₅₁H₃₂N₄ = 700.85) 3-96 m/z =764.29 (C₅₆H₃₆N₄ = 764.93) 3-97 m/z = 700.29 (C₅₃H₃₆N₂ = 700.89 3-98 m/z= 576.26 (C₄₃H₃₂N₂ = 576.74) 3-99 m/z = 701.28 (C₅₂H₃₅N₃ = 701.87) 3-100m/z = 761.28 (C₅₇H₃₅N₃ = 761.93)

Otherwise, the synthesis examples of the present invention representedby Formulas (1) and (2) have been described, but these are all based onthe Buchwald-Hartwig cross coupling reaction, Suzuki cross-couplingreaction, Intramolecular acid-induced cyclization reaction (J. mater.Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction(Org. Lett. 2011, 13, 5504), Grignard reaction, Cyclic Dehydrationreaction and PPh₃-mediated reductive cyclization reaction (J. Org. Chem.2005, 70, 5014.), and those skilled in the art will readily understandthat the above reaction proceeds even when, besides the substituentspecified in the specific synthesis example, other substituents (R¹ toR⁵, Ar¹ to Ar⁴, L¹ to L², X¹ to X²) defined in Formula (1) are bonded.

For example, Sub 1+Sub 2->Final Products 1 reaction in Reaction Scheme1, the synthetic reaction of Sub 2 in Reaction Scheme 2, Sub 3+Sub4->Final Products 2 reaction in Reaction Scheme 3 are all based on theBuchwald-Hartwig cross coupling reaction, and Sub 3-2+Sub 3-3->Sub 3-4reaction in Reaction Scheme 4 is based on the Suzuki cross-couplingreaction, and Sub 3-4->Sub 3 in Reaction Scheme 4 is based on thePPh₃-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70,5014.) The above reactions will proceed even if a substituent notspecifically mentioned is bonded.

Evaluation of Manufacture of Organic Electric Element Example 1)Manufacture and Evaluation of Red Organic Light Emitting Diode

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) wasvacuum-deposited to form a hole injection layer with a thickness of 60nm, andN,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter will be abbreviated as NPB) was vacuum-deposited to form ahole transport layer with a thickness of 60 nm. On the hole transportlayer, a mixture of the compounds represented by Formulas (1) and (2) asa host in a ratio of 3:7 was used as a host, and as a dopant, anemitting layer with a thickness of 30 nm was deposited on the holetransport layer by doping (piq)₂Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] with a weight of95:5. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAlq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and tris(8-quinolinol)aluminum(hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nmas an electron transport layer. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of2500 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

Comparative Examples 1 to 3

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the compound represented by Formula (2) wasused as a host alone.

Comparative Example 4

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 1 was used as ahost alone.

Comparative Example 5

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 2 was used as ahost alone.

Comparative Example 6

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 3 was used as ahost alone.

Comparative Example 7

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 4 was used as ahost alone.

Comparative Example 8

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that comparative compound 1 and 2 were mixed andused as a host.

Comparative Example 9

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that comparative compound 3 and 4 were mixed andused as a host.

TABLE 6 Current Brightness Lifetime First host Second host VoltageDensity (cd/m²) Efficiency T(95) comparative — compound(3-6) 6.6 19.12500.0 13.1 100.3 example(1) comparative — compound(3-61) 6.8 19.52500.0 12.8 98.8 example(2) comparative — compound(3-74) 6.9 20.2 2500.012.4 101.2 example(3) comparative — comparative 7.3 22.5 2500.0 11.176.3 example(4) compound 1 comparative — comparative 7.2 21.7 2500.011.5 78.9 example(5) compound 2 comparative — comparative 7.1 21.02500.0 11.9 82.4 example(6) compound 3 comparative — comparative 7.422.3 2500.0 11.2 74.5 example(7) compound 4 comparative comparativecomparative 6.5 14.8 2500.0 16.9 105.9 example(8) compound 1 compound 2comparative comparative comparative 6.4 13.7 2500.0 18.3 106.1example(9) compound 3 compound 4 example(1) compound(1-4′) compound(3-6)5.6 8.7 2500.0 28.7 129.0 example(2) compound(1-10′) compound(3-6) 5.98.8 2500.0 28.3 129.9 example(3) compound(1-16′) compound(3-6) 5.5 8.52500.0 29.4 127.1 example(4) compound(1-21′) compound(3-6) 5.6 7.82500.0 31.9 132.0 example(5) compound(1-33′) compound(3-6) 5.9 8.22500.0 30.6 131.6 example(6) compound(1-45′) compound(3-6) 5.8 8.12500.0 30.7 132.0 example(7) compound(1-48′) compound(3-6) 5.6 7.82500.0 32.2 132.4 example(8) compound(1-50′) compound(3-6) 5.8 7.72500.0 32.3 133.0 example(9) compound(1-55′) compound(3-6) 5.9 7.62500.0 32.9 132.9 example(10) compound(1-56′) compound(3-6) 5.7 7.72500.0 32.7 132.5 example(11) compound(1-4′) compound(3-7) 5.8 10.92500.0 23.0 120.8 example(12) compound(1-10′) compound(3-7) 6.0 10.82500.0 23.2 120.4 example(13) compound(1-16′) compound(3-7) 5.6 11.02500.0 22.7 120.5 example(14) compound(1-21′) compound(3-7) 5.6 10.12500.0 24.6 121.9 example(15) compound(1-33′) compound(3-7) 5.6 10.22500.0 24.4 122.8 example(16) compound(1-45′) compound(3-7) 5.6 9.72500.0 25.6 121.4 example(17) compound(1-48′) compound(3-7) 5.7 9.32500.0 26.8 124.5 example(18) compound(1-50′) compound(3-7) 5.8 9.62500.0 26.1 124.2 example(19) compound(1-55′) compound(3-7) 5.7 9.52500.0 26.5 124.8 example(20) compound(1-56′) compound(3-7) 5.7 9.62500.0 26.0 123.1 example(21) compound(1-4′) compound(3-8) 5.8 11.12500.0 22.6 120.4 example(22) compound(1-10′) compound(3-8) 6.0 11.32500.0 22.1 120.6 example(23) compound(1-16′) compound(3-8) 5.9 11.12500.0 22.4 120.1 example(24) compound(1-21′) compound(3-8) 5.6 10.22500.0 24.4 122.3 example(25) compound(1-33′) compound(3-8) 5.6 9.82500.0 25.5 122.4 example(26) compound(1-45′) compound(3-8) 5.7 10.22500.0 24.6 121.9 example(27) compound(1-48′) compound(3-8) 5.9 9.52500.0 26.4 123.4 example(28) compound(1-50′) compound(3-8) 5.7 9.52500.0 26.3 123.5 example(29) compound(1-55′) compound(3-8) 5.8 9.32500.0 26.8 124.3 example(30) compound(1-56′) compound(3-8) 5.9 9.52500.0 26.3 124.8 example(31) compound(1-4′) compound(3-9) 5.5 10.82500.0 23.2 120.6 example(32) compound(1-10′) compound(3-9) 5.9 11.22500.0 22.4 120.3 example(33) compound(1-16′) compound(3-9) 5.8 11.12500.0 22.6 120.1 example(34) compound(1-21′) compound(3-9) 5.8 10.02500.0 25.0 121.2 example(35) compound(1-33′) compound(3-9) 5.7 10.32500.0 24.4 122.8 example(36) compound(1-45′) compound(3-9) 5.6 9.62500.0 25.9 122.9 example(37) compound(1-48′) compound(3-9) 5.6 9.32500.0 26.8 125.0 example(38) compound(1-50′) compound(3-9) 5.9 9.62500.0 26.2 124.1 example(39) compound(1-55′) compound(3-9) 5.7 9.42500.0 26.5 124.0 example(40) compound(1-56′) compound(3-9) 5.7 9.42500.0 26.7 124.9 example(41) compound(1-4′) compound(3-15) 5.6 10.62500.0 23.7 120.0 example(42) compound(1-10′) compound(3-15) 5.9 11.02500.0 22.7 120.6 example(43) compound(1-16′) compound(3-15) 5.8 10.72500.0 23.5 120.9 example(44) compound(1-21′) compound(3-15) 5.8 10.32500.0 24.2 122.4 example(45) compound(1-33′) compound(3-15) 5.6 10.22500.0 24.6 121.7 example(46) compound(1-45′) compound(3-15) 5.8 10.12500.0 24.8 122.3 example(47) compound(1-48′) compound(3-15) 5.7 9.62500.0 26.2 123.5 example(48) compound(1-50′) compound(3-15) 5.8 9.52500.0 26.3 123.5 example(49) compound(1-55′) compound(3-15) 5.9 9.32500.0 27.0 123.2 example(50) compound(1-56′) compound(3-15) 5.7 9.52500.0 26.2 123.7 example(51) compound(1-4′) compound(3-37) 5.6 10.52500.0 23.8 120.5 example(52) compound(1-10′) compound(3-37) 5.7 11.22500.0 22.3 120.6 example(53) compound(1-16′) compound(3-37) 5.6 10.62500.0 23.5 121.0 example(54) compound(1-21′) compound(3-37) 6.0 10.02500.0 25.1 122.5 example(55) compound(1-33′) compound(3-37) 5.5 10.32500.0 24.2 122.4 example(56) compound(1-45′) compound(3-37) 5.7 9.72500.0 25.7 122.3 example(57) compound(1-48′) compound(3-37) 6.0 9.52500.0 26.2 124.7 example(58) compound(1-50′) compound(3-37) 5.9 9.32500.0 26.9 123.6 example(59) compound(1-55′) compound(3-37) 5.9 9.42500.0 26.7 124.2 example(60) compound(1-56′) compound(3-37) 5.6 9.42500.0 26.6 124.0 example(61) compound(1-4′) compound(3-46) 5.5 11.32500.0 22.2 120.9 example(62) compound(1-10′) compound(3-46) 5.6 10.82500.0 23.2 120.2 example(63) compound(1-16′) compound(3-46) 5.8 11.02500.0 22.7 120.7 example(64) compound(1-21′) compound(3-46) 5.6 10.12500.0 24.8 122.5 example(65) compound(1-33′) compound(3-46) 5.9 9.82500.0 25.5 121.1 example(66) compound(1-45′) compound(3-46) 5.5 10.22500.0 24.5 121.8 example(67) compound(1-48′) compound(3-46) 5.8 9.32500.0 26.8 124.3 example(68) compound(1-50′) compound(3-46) 5.7 9.32500.0 26.9 124.6 example(69) compound(1-55′) compound(3-46) 5.6 9.42500.0 26.6 124.8 example(70) compound(1-56′) compound(3-46) 5.9 9.32500.0 26.8 124.8 example(71) compound(1-4′) compound(3-50) 5.9 11.22500.0 22.3 120.7 example(72) compound(1-10′) compound(3-50) 5.9 10.82500.0 23.1 120.1 example(73) compound(1-16′) compound(3-50) 5.8 11.22500.0 22.2 120.7 example(74) compound(1-21′) compound(3-50) 5.8 10.32500.0 24.2 122.5 example(75) compound(1-33′) compound(3-50) 5.5 9.82500.0 25.5 122.1 example(76) compound(1-45′) compound(3-50) 5.5 10.22500.0 24.5 121.6 example(77) compound(1-48′) compound(3-50) 5.7 9.52500.0 26.2 123.4 example(78) compound(1-50′) compound(3-50) 6.0 9.42500.0 26.6 123.2 example(79) compound(1-55′) compound(3-50) 5.8 9.62500.0 26.1 124.5 example(80) compound(1-56′) compound(3-50) 5.6 9.32500.0 26.9 124.0 example(81) compound(1-4′) compound(3-61) 5.9 9.42500.0 26.5 120.1 example(82) compound(1-10′) compound(3-61) 5.5 9.52500.0 26.4 120.1 example(83) compound(1-16′) compound(3-61) 6.0 9.32500.0 26.8 120.8 example(84) compound(1-21′) compound(3-61) 6.0 9.22500.0 27.1 121.6 example(85) compound(1-33′) compound(3-61) 5.5 9.22500.0 27.1 122.7 example(86) compound(1-45′) compound(3-61) 5.6 9.02500.0 27.8 121.9 example(87) compound(1-48′) compound(3-61) 5.8 8.62500.0 29.0 123.0 example(88) compound(1-50′) compound(3-61) 5.8 8.62500.0 29.2 123.7 example(89) compound(1-55′) compound(3-61) 5.6 8.82500.0 28.4 124.6 example(90) compound(1-56′) compound(3-61) 5.9 8.82500.0 28.5 124.0 example(91) compound(1-4′) compound(3-74) 5.9 10.92500.0 23.0 120.3 example(92) compound(1-10′) compound(3-74) 5.6 10.62500.0 23.5 120.1 example(93) compound(1-16′) compound(3-74) 5.8 11.12500.0 22.5 120.2 example(94) compound(1-21′) compound(3-74) 5.5 10.32500.0 24.3 121.3 example(95) compound(1-33′) compound(3-74) 5.7 10.32500.0 24.2 122.6 example(96) compound(1-45′) compound(3-74) 6.0 10.02500.0 25.1 121.8 example(97) compound(1-48′) compound(3-74) 6.0 9.52500.0 26.5 124.0 example(98) compound(1-50′) compound(3-74) 5.6 9.42500.0 26.5 123.3 example(99) compound(1-55′) compound(3-74) 5.6 9.32500.0 26.8 124.0 example(100) compound(1-56′) compound(3-74) 5.9 9.62500.0 26.1 124.3

As can be seen from the results of Table 6, when the organic electricelement material of the present invention represented by Formulas (1)and (2) is mixed and used as a phosphorescent host (Examples 1 to 100),it was confirmed that the driving voltage, efficiency, and life spanwere significantly improved as compared with the element (comparativeexamples 1 to 7) using a single material. More specifically, inComparative Examples 1 to 7, wherein the compounds of the presentinvention represented by Formula (2) and comparative compounds 1 to 4are used alone as a phosphorescent host, Comparative Examples 1 to 3using the compounds (3-6, 3-61, and 3-74) of the present invention hadhigher efficiency and longer life span than Comparative Examples 4 to 7using the comparative compound.

Also, Comparative Example 8 and 9 wherein Comparative Compound 1 and 2or Comparative Compound 3 and 4 were mixed and used as a phosphorescenthost were found to exhibit higher efficiency than Comparative Examples 1to 7 using the single substance. Comparing Comparative Example 8 with 9,Comparative Example 9 using a mixture containing a polycyclic compoundhaving a different heteroatom (N, S) among the 5-membered compounds hadhigher efficiency than Comparative Example 8 mixed a 5-memberedheterocyclic compound having the same nitrogen atom. And it wasconfirmed that Example 1 to 100 using the mixture of the compound ofFormula (1) and (2) as a host exhibited remarkably high efficiency andlong life span than the Comparative Example 1 to 9.

On the basis of the above experimental results, the inventors of thepresent invention have found that, in the case of a mixture of thesubstance of Formulas (1) and (2), they have novel characteristics otherthan those for the respective materials, and have measured the PLlifetime using the substance of Formula (1), the substance of Formula(2), and the mixture of the present invention. As a result, it wasconfirmed that a new PL wavelength was formed when the compounds ofFormulas (1) and (2) were mixed, and the decreasing and disappearingtime of the newly formed PL wavelength increased from about 60 times toabout 360 times compared to the reduction and disappearance times ofsubstances Formula (1) and (2), respectively. It is considered whenmixed with the compound of the present invention, not only electrons andholes are moved through the energy level of each substance, but also theefficiency and life span are increased by electron, hole transport orenergy transfer by a new region (exciplex) having a new energy levelformed due to mixing. As a result, when the mixture of the presentinvention is used, the mixed thin film is an important example showingexciplex energy transfer and light emitting process.

The reason why the combination of the present invention is superior toComparative Examples 8 to 9 in which a comparative compound is used as aphosphorescent host is that the high T1 and high LUMO energy valuesimprove the electron blocking ability and allow more holes to be movedto the emitting layer more quickly and easily when a compoundrepresented by Formula (1) having a strong hole property is mixed with apolycyclic compound represented by Formula (2), which is characterizednot only by electron but also by hole stability and high T1. As aresult, the charge balance in the emitting layer of holes and electronsis increased, so that light emission is well performed inside theemitting layer rather than at the interface of the hole transport layer,and therefore the deterioration in the HTL interface is also reduced,thereby maximizing the driving voltage, efficiency and life span of thedevice.

Among the compounds represented by Formula (1), it has been confirmedthat Dibenzofuran substituted compounds exhibits the best results interms of the driving voltage, the efficiency and the lifetime, andDibenzothiophen substituted compounds are also excellent in terms ofefficiency due to their high refractive index. That is, it is concludedthat the combination of Formula (1) and Formula (2) is electrochemicallysynergistic to improve the performance of the device as a whole.

Example 2) Manufacture and Evaluation of Red Organic Light EmittingDiode by Mixing Ratio

TABLE 7 Mixing ratio (first host:second Current Brightness LifetimeFirst host Second host host) Voltage Density (cd/m2) Efficiency T(95)example(101) compound(1-33′) compound(3-61) 2:8 5.5 9.1 2500.0 27.4123.0 example(102) compound(1-33′) compound(3-61) 3:7 5.5 9.2 2500.027.1 122.7 example(103) compound(1-33′) compound(3-61) 4:6 5.7 9.72500.0 25.9 120.1 example(104) compound(1-33′) compound(3-61) 5:5 6.010.8 2500.0 23.1 119.4 example(105) compound(1-50′) compound(3-6) 2:85.7 7.4 2500.0 33.6 133.6 example(106) compound(1-50′) compound(3-6) 3:75.8 7.7 2500.0 32.3 133.0 example(107) compound(1-50′) compound(3-6) 4:66.1 8.1 2500.0 30.7 130.5 example(108) compound(1-50′) compound(3-6) 5:56.3 8.8 2500.0 28.4 128.4

As shown in Table 7, the mixture of the compound of the presentinvention was measured by fabricating the device in (2:8, 3:7, 4:6,5:5). To explain the results in detail, in the result of the mixture ofthe compound 1-33′ and 3-61, the results of the driving voltage, theefficiency and the life span were similarly excellent at 2:8 and 3:7,but as the ratio of the first host increases, such as 4:6 and 5:5, theresults of the driving voltage, the efficiency and the life span aregradually decreased, this was also the same in the result of the mixtureof the compound 1-50′ and 3-6. This can be explained by the fact thatthe charge balance in the emitting layer is maximized when anappropriate amount of the compound represented by Formula (1) havingstrong hole properties such as 2:8 and 3:7 is mixed.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis ofthe accompanying claims, and it shall be construed that all of thetechnical ideas included within the scope equivalent to the claimsbelong to the present invention.

What is claimed is:
 1. An organic electric element comprising a firstelectrode, a second electrode, and an organic material layer formedbetween the first electrode and the second electrode, wherein theorganic material layer comprises an emitting layer, and the emittinglayer is a phosphorescent light emitting layer comprising a first hostcompound represented by Formula (1) and a second host compoundrepresented by Formula (2):

wherein: 1) Ar¹, Ar², Ar³ and Ar⁴ are each independently selected fromthe group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one hetero atom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; 2) C and e areeach independently integers of 0 to 10, d is an integer of 0 to 2, andR³, R⁴ and R⁵ are, being the same or different from each other, eachindependently selected from the group consisting of deuterium; halogen;a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si and P; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)) (whereinL′ is selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic,and R_(a) and R_(b) are independently selected from the group consistingof a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group containing at least one hetero atom of O, N, S, Si,and P), wherein in case c and e are 2 or more, R³, R⁴ and R⁵ are each inplural being the same or different and a plurality of R³ or a pluralityof R⁴ or a plurality of R⁵ combine to each other to form a ring; 3) L¹,L², L³ and L⁴ are each independently selected from the group consistingof a single bond; a C₆-C₆₀ arylene group; and a fluorenylene group; afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;and a C₂-C₆₀ heterocyclic group; 4) A and B are each independently aC₆-C₂₀ aryl group or a C₂-C₂₀ heterocyclic group, with the proviso thatboth A and B are not a C₆ aryl group at the same time; 5) i and j areeach independently 0 or 1, wherein i+j is 1 or more, and where i or j is0, it means a direct bond, 6) X¹ and X² are NR′, wherein R′ is selectedfrom the group consisting of hydrogen, a C₆-C₆₀ aryl group, a fluorenylgroup, a C₃-C₆₀ heterocyclic group, and a C₁-C₅₀ alkyl group, whereinthe aryl group, fluorenyl group, arylene group, heterocyclic group,fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxygroup may be substituted with one or more substituents selected from thegroup consisting of deuterium; halogen; a silane group substituted orunsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxanegroup; boron group; germanium group; cyano group; nitro group;-L′-N(R_(a))(R_(b)); a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group;C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenylgroup; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀arylalkyl group; and C₈-C₂₀ arylalkenyl group, wherein the substituentsmay combine each other and form a saturated or unsaturated ring, whereinthe term ‘ring’ means C₃-C₆₀ aliphatic ring or C₆-C₆₀ aromatic ring or aC₂-C₆₀ heterocyclic ring or a fused ring formed by the combination ofthereof.
 2. The organic electric element according to claim 1, whereinthe first host compound represented by Formula (1) is represented by anyone of the following Formulas (3) to (5):

wherein: 1) L¹, L³, L⁴, Ar² and Ar³ are the same as defined in theclaim, 2) X³ is 0 or S, 3) a is an integer of 0 to 4, b is an integer of0 to 3, and R¹ and R² are the same or different from each other and areeach independently selected from the group consisting of deuterium;halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si and P; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; aC₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));or in case a and b are 2 or more, R¹ and R² are each in plural being thesame or different, and a plurality of R¹ or a plurality of R² combine toeach other to form a ring.
 3. The organic electric element according toclaim 1, wherein the compound represented by Formula (1) is representedby any one of the following Formulas (6) to (14):

wherein: 1) L¹, L³, L⁴, Ar² and Ar³ are the same as defined in theclaim, 2) a is an integer of 0 to 4, b is an integer of 0 to 3, and R¹and R² are the same or different from each other, and are eachindependently selected from the group consisting of deuterium; halogen;a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si and P; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or incase a and b are 2 or more, R¹ and R² are each in plural being the sameor different, and a plurality of R¹ or a plurality of R² combine to eachother to form a ring.
 4. The organic electric element according to claim1, wherein the first host compound represented by Formula (1) isrepresented by any one of the following Formulas (15) to (23):

wherein: 1) L¹, L³, L⁴, Ar² and Ar³ are the same as defined in claim 1,2) a is an integer of 0 to 4, b is an integer of 0 to 3, and R¹ and R²are the same or different from each other, and are each independentlyselected from the group consisting of deuterium; halogen; a C₆-C₆₀ arylgroup; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at leastone heteroatom of O, N, S, Si and P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; aC₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or in case a and b are 2or more, R¹ and R² are each in plural being the same or different, and aplurality of R¹ or a plurality of R² combine to each other to form aring.
 5. The organic electric element according to claim 1, wherein Ar¹,Ar² and Ar³ in Formula (1) are all C₆-C₂₄ aryl groups, and L¹, L³ and L⁴are single bonds or all C₆-C₂₄ aryl groups.
 6. The organic electricelement according to claim 1, wherein the compound represented byFormula (1) is represented by any one of the following Formulas (24) to(26):

wherein: 1) L¹, L³, L⁴, Ar² and Ar³ are the same as defined in claim 1,2) Ar⁵ and Ar⁶ are each independently selected from the group consistingof a C₆-C₆₀ aryl group; a C₂-C₆₀ heterocyclic group including at leastone heteroatom of O, N, S, Si and P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; aC₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)).
 7. The organic electricelement according to claim 1, wherein L¹, L³ and L⁴ in Formula (1) areeach selected from the group consisting of the following Formulas (A-1)to (A-12):

wherein: 1) A′, c′, d′ and e′ are each independently integers of 0 to 4;b′ is an integer of 0 to 6; f′ and g′ are each independently integers of0 to 3; and h′ is an integer of 0 to 1, 2) R⁶, R⁷ and R⁸ are the same ordifferent from each other, and are each independently selected from thegroup consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenylgroup; a C₂-C₆₀ heterocyclic group including at least one heteroatom ofO, N, S, Si and P; a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; aC₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group;and -L′-N(R_(a))(R_(b)); or in case f ‘and g’ are 2 or more, R⁶, R⁷ andR⁸ are each in plural being the same or different from each other, and aplurality of R⁶ or a plurality of R⁷ or adjacent R⁶ and R⁷ may combineto each other to form an aromatic or a heteroaromatic ring, 3) Y is NR′,0, S or CR′R″, wherein R′ and R″ are the same as defined in the claim,4) Z¹, Z² and Z³ are each independently CR′ or N, wherein at least oneis N.
 8. The organic electric element according to claim 1, wherein atleast one of L¹, L³, and L⁴ in Formula (1) is substituted on am(meta)-position.
 9. The organic electric element according to claim 1,wherein the second host compound represented by Formula (2) comprises acompound represented by the following Formula (27) or (28):

wherein R³, R⁴, R⁵, Ar⁴, L², c, d, e, A, B, X¹ and X² are the same asdefined in the claim.
 10. The organic electric element according toclaim 1, wherein A and B in Formula (2) are selected from the groupconsisting of the following Formulas (B-1) to (B-7):

wherein: 1) Z⁴ to Z⁵⁰ are each independently CR′ or N, 2) R′ is the sameas defined in the claim, 3) * indicates the position to be condensed.11. The organic electric element according to claim 1, wherein thesecond host compound represented by Formula (2) includes a compoundrepresented by any of the following Formulas (29) to (48):

wherein Ar⁴, L², X¹, X², R³, R⁴, R⁵, c, d, and e are the same as definedin the claim.
 12. The organic electric element according to claim 1,wherein the second host compound represented by Formula (2) comprisesany of compounds represented by the following Formulas (49) and (53):

wherein R³, R⁴, R⁵, L², Ar⁴, c, d, e, A, B, R′ and R″ are the same asdefined in the claim.
 13. The organic electric element according toclaim 1, wherein the first host compound represented by Formula (1) isone of the following Compounds 1-1′ to 1-82′:


14. The organic electric element according to claim 1, wherein thesecond host compound represented by Formula (2) is one of the followingcompounds:


15. The organic electronic element of claim 1, further comprising atleast one hole transporting band layer between the first electrode andthe emitting layer, wherein the hole transporting band layer includes ahole transport layer, an emitting auxiliary layer, or both the layers,and the hole transporting band layer includes a compound represented byFormula (1).
 16. The organic electric element according to claim 1,wherein the compounds represented by Formula (1) and (2) are mixed in aratio of 1:9 to 9:1 to be included in the emitting layer.
 17. Theorganic electric element according to claim 1, wherein the compoundrepresented by Formula (1) and (2) are mixed in a ratio of 1:9 to 5:5 tobe included in the emitting layer.
 18. The organic electric elementaccording to claim 1, wherein the compound represented by Formula (1)and (2) are mixed in a ratio of 2:8 or 3:7 to be included in theemitting layer.
 19. A display device comprising the organic electricelement of claim 1 and a control part driving the display device.
 20. Adisplay device according to claim 19, wherein the organic electronicelement is an OLED, an organic solar cell, an organic photo conductor(OPC), organic transistor (organic TFT), or an element for monochromicor white illumination.